The beginnings of the principality of Moldavia in 1359 are somewhat shrouded in mystery, but several important leaders shaped the political, economic, and cultural position of the principality, including Peter I Muşat, Alexander I, and Stephen III. From the second half of the fourteenth century onward, Moldavia found itself at the crossroads of different cultures, among them Western and Central European, Byzantine, Slavic, and even Islamic. The networked position of this Carpathian principality enabled it to foster political, military, economic, and cultural ties with its closer and more distant neighbours. Contact and exchange facilitated the local assimilation of elements from various traditions that gave rise to distinct cultural and visual forms in Moldavia. This visual syncretism is most evident in the artistic and architectural spheres, both secular and ecclesiastical. The numerous fortifications of the principality and the dozens of fortified monasteries exhibit design and stylistic forms drawn from distinct traditions and adapted alongside local models. These structures were strategically erected along the perimeter of Moldavia in efforts to ensure the principality's protection from all sides. The secular and the religious spheres thus complemented each other and worked to further the protection of the land.

But it was especially from Stephen's rule in 1457—just a few years after the fall of Constantinople to the Ottomans in 1453—that Moldavia as a polity began to assume a crucial role in the continuation and transformation of Byzantine traditions and legacies while serving as a “shield” for the rest of Europe in the face of the rapidly advancing Tatar forces and expanding Ottoman Empire. After the death of Stephen III, Moldavia entered a period of turmoil. His immediate heirs, Bogdan III (r. 1504–1517) and Stephen IV (r. 1517–1527) were unable to maintain harmony and peace. They struggled against outside threats and internally against members of the high nobility who often rose against them. Outside threats from neighbours and the Ottomans were ongoing and intensified during the initial years of the sixteenth century. In 1505, for example, Radu the Great (r. 1495–1508) led his Wallachian troops into Moldavia to take over the principality but was defeated. The following year, in 1506, the Polish armies, under Sigismund I, attacked Moldavia and advanced as far as Botoşani but they were eventually forced to retreat.